Lakeside or sky-high? Take your pick among Chicago's most-expensive homes

(Crain's) — Home shoppers looking at the very top of the upper bracket have a lot of choices these days.

Those with suburban tastes can pick from Michael Jordan's Highland Park estate, which was listed in February for $29 million, or a recently built French Provincial on Winnetka's lakefront for nearly $16 million.

Urbanites who can afford an eight-digit price tag, meanwhile, have two options: a three-floor condominium on North Michigan Avenue owned by actor Vince Vaughn, who is asking $18.4 million, or an unfinished condo on the 89th floor of the Trump International Hotel & Tower, listed for $32 million — more than any other property in the Chicago area.

“The word is out there right now: You just have to find somebody who is willing to pay this type of money, ” says Coldwell Banker agent Chezi Rafaeli, who is listing the 14,260-square-foot condo for developer Donald Trump.

He makes it sound easy, but that type of buyer doesn't come along every day: Only two homes here have sold for more than $10 million in the past five years, and both sales closed in 2007, according to a search of a database managed by Midwest Real Estate Data LLC.

In all, seven Chicago-area homes are listed for more than $10 million, according to MRED data. The list of the top 10 most expensive homes in the Chicago area includes a foreclosed Lake Forest estate listed for $12 million and a modernist Keck & Keck-designed home in Lake Bluff owned by the estate of the Blair family — as in William Blair & Co.

Marketing properties in that price range offers challenges to brokers, who will often contact corporate executives directly after hearing that they are relocating to Chicago.

“We reach out to their travel service, relocation services, anybody who's in the know,” says @properties agent Steven Aisen, who has the listing on the Winnetka property, a seven-bedroom home with a pool and 130 feet of Lake Michigan frontage.

Though he won't rule out a foreign buyer, Mr. Aisen says he targets three groups of prospects for his top-end North Shore homes: the North Shore native looking to upsize, the city dweller aiming to move out and the newly transplanted executive.

Once buyers are on the hook, reeling them in isn't easy. Uber-wealthy buyers — who are often able to pay cash, eliminating one potential complication — can be shrewd negotiators. And many wealthy sellers can afford to be patient.

“You have to understand how to negotiate with these people,” says Tere Proctor, an agent at Koenig & Strey. “If they're interested, it's either you make a deal or not.”